Phenylpyruvic acid → HCID 49854209, compound
Reaction equation
[C:1]1([CH2:7][C:8](=[O:12])[C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[CH2:35]([NH2:42])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>C(Cl)Cl>[CH2:35]([NH:42][C:9](=[O:11])[C:8](=[O:12])[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
A suspension of phenylpyruvic acid (2.1 g; 12.8 mmol) in DCM (50 ml) was cooled to 0° C. Then EDCl (3 g, 15.6 mmol) and HOBt (0.2 g, 1.5 mmol) were added successively. The resulted solution was cooled to −5° C. and then heptylamine (1.5 g, 13 mmol) was added dropwise at temperature below 0° C. Upon the addition the ice bath was removed and the reaction mixture was stirred overnight at room temperature. The reaction mixture was poured into 1% aqueous hydrochloric acid solution (30 ml). The DCM phase was washed with water and concentrated in vacuum. The crude product was chromatographed on a silica gel column using ethylacetate/hexane (1:2) as eluent to provide the title compound (0.8 g, 24% yield).
Workup
- temperatureThe resulted solution was cooled to −5° C.
- customwas removed
- additionThe reaction mixture was poured into 1% aqueous hydrochloric acid solution (30 ml)
- washThe DCM phase was washed with water
- concentrationconcentrated in vacuum
- customThe crude product was chromatographed on a silica gel column
Sources & evidence
- ORD record
- ord-8694c14795904f4aad55cd791535e2c6
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08816102B2
Reaction notes
Loading…